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Vacation rentals in Medstead

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Medstead

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Tiny home in Froxfield
4.82 out of 5 average rating, 133 reviews

Romantic OffGrid Cabin | Stargazing & Valley Views

Featured in The Guardian and The Times Top 10 UK Off-Grid Stays. Wake to sunrise over the South Downs in this secluded hilltop off-grid cabin overlooking the whole of the South Downs National park. Experience total serenity under star-filled skies with the warmth of a wood-burning stove enhancing the peaceful ambiance. Our off-grid cabin offers tranquility whilst still being close to cosy pubs, historic towns and scenic walks. Dog Friendly. It’s the perfect place to disconnect and recharge.

Superhost
A rustic cabin with a dark metal roof features wooden siding and large glass windows. An outdoor deck includes comfortable seating and a fire pit. The cozy hot tub, partially visible through curtains, invites relaxation, surrounded by greenery and the warm glow of evening lights.
Farm stay in Headbourne Worthy
4.96 out of 5 average rating, 365 reviews

A Unique Farm Retreat

There’s something magical about The Granary. Set in acres of farmland with spectacular sunrises and sunsets, The Granary brims with rustic charm. A dreamy hideaway with an outdoor copper bath and wood fired hot tub. An idyllic get-away-from-it-all yet only 3 miles to historic Winchester. Soak amid hot water, steam and fresh air surrounded by nature and birdsong, enjoy magnificent sunsets from the ‘Sundowner’ or cosy up toasting marshmallows over the fire pit - a perfect escape to unwind.

Top guest favorite
Hut in Winchester
4.98 out of 5 average rating, 634 reviews

The Pigsty

The Pigsty is Winchester's first luxury woodland hideaway, with beautiful views of Vale Farm. Less than 2.5 miles from the historic centre of Winchester, this peaceful retreat is perfect for those looking to visit the city, or escape for some peace. The Pigsty’s domed design with wooden interior has a roll top bath, cosy open plan living space and decking area to enjoy dinner with sunset views. Just a few minutes walk from the famous Clarendon Way, and a 30 minute walk to the city centre.

Guest favorite
An indoor space features a beautifully crafted wine barrel hot tub, surrounded by rustic wooden walls and beams. A cozy seating area with unique decor complements the intimate atmosphere. Natural light filters through framed artwork, enhancing the inviting environment.
Shepherd’s hut in Medstead
4.95 out of 5 average rating, 792 reviews

Wagon in the Woods & Wine Barrel Hot Tub

A cosy wagon and a hot tub in a giant wine barrel! Nestled in the Hampshire countryside. Features inside include a double bed, trap-door bath, toilet, and large ‘wagon wheel’ window with stunning views. Outdoors is the Wild Cherry Barn with chiminea fireplace and a saloon seating area with pizza oven and campfire with BBQ grill. The Wagon in the Woods is a bespoke, self-contained little place in the country with a private woodland, ideal for those wanting a tranquil and restful getaway.

Top guest favorite
A rustic oak-framed barn is nestled among trees, showcasing a sloped roof and large windows. Gravel pathways lead to the entrance, framed by potted plants. The structure is surrounded by open space, offering a serene rural setting.
Home in Winchester
4.94 out of 5 average rating, 393 reviews

Oak Framed Barn with Tennis Court

A stylish secluded, two storey, oak framed barn with tennis court, 4 miles from Winchester. Homely space with two bedrooms plus a sofa bed (upon request) and ground floor open plan living area. Super fast WiFi. The Barn adjoins the Watercress Way and stands separately in the grounds with views over open Hampshire fields. Nearest neighbour c.1 mile away but there is loads to do in the area with an abundance of country pubs, one or two within walking distance and beaches within 50 minutes

Top guest favorite
An outdoor deck features a wooden table set for two with a folding chair and a cushioned seat. Double doors lead into the hangar, framed by a surrounding landscape of arable fields and wildflower meadows under clear blue skies.
Hut in Braishfield
4.99 out of 5 average rating, 386 reviews

The Hangar - countryside views, seclusion & peace.

The Farley Hangar is a peaceful space with far reaching views of Hampshire's woodlands and the Isle of Wight. Located on our family farm and private airstrip in the Test Valley. Winchester, Romsey and Stockbridge are just 20 mins away. On the doorstep of numerous cycle routes and footpaths including the Claredon Way (Sals-Win). King size bed & full-size bath with rain shower. From your private deck with log burner you will see various wildlife species and watch the stars at night.

Guest favorite
The exterior of the cottage features a striking A-frame design with large glass doors. Lush greenery surrounds the property, including several trees and well-maintained grass. A patio umbrella offers shade over the outdoor seating area, creating an inviting space for relaxation.
Cottage in Ropley
4.91 out of 5 average rating, 132 reviews

Historic 16th Century thatched cottage, Hampshire

Right in the middle of Jane Austen country, this famous chocolate box 16th Century Grade II listed cottage, the oldest house in the village, is chocca-block full of history. It was home to the Archbishop of Canterbury, Queen Victoria's right-hand man, who not only christened and crowned the Queen but then went on to marry her Prince Albert. Set in the picture-perfect Hampshire village full of thatched cottages and surrounded by gorgeous walks it is the perfect country retreat!

Guest favorite
An A-frame structure is framed by trees and surrounded by blooming bluebells. Light filters through the open front, illuminating the interior where a seating area is presented. The natural setting offers a serene escape, with vibrant flowers in the foreground enhancing the tranquil scene.
Hut in Ovington
4.97 out of 5 average rating, 165 reviews

The Glade at Ladyhill Vineyard near Winchester

Nestled on the edge of an ancient wood in South Downs National Park and with fantastic views over Ladyhill Vineyard and the Hampshire countryside The Glade has a cosy A-Frame to grab a good night sleep, a separate shower room with flushable loo to keep you fresh and a kitchen equip-for-easy glamping. Relax and admire the views, BBQ on the fire pit, spot deer and hare or stroll down the river Itchen to The Bush gastro pub. You’ll return home totally refreshed!

Top guest favorite
Loft in Upper Wield
4.97 out of 5 average rating, 144 reviews

Lovely one bed flat with free parking on premises

A small but perfectly formed one bedroom flat in a rural location. The Annex has a small kitchen with hob, cooker and microwave. There is a table for eating. One double bed and a shower room. We have good broadband and there is parking on the property. The village has a great pub within walking distance and plenty of lovely walks. We are about 11 miles from Winchester and 3 miles from Jane Austen's Chawton. Our stairs into the flat are steep and narrow.

Guest favorite
A couple relaxes in a bubbling outdoor hot tub, holding glasses, with a scenic view of lush green fields and trees in the background. A champagne bottle sits in an ice bucket beside them, enhancing the tranquil atmosphere.
Shepherd’s hut in Chessington
4.98 out of 5 average rating, 356 reviews

The Ultimate Couples Retreat | 30 Mins from London

This countryside retreat is the perfect romantic escape, just a 35 minute taxi/train ride minutes from London. Unwind in your private luxury hot tub, sip on a complimentary bottle Champagne under the stars, and wake up to breathtaking views of rolling fields and wildlife. Our handcrafted shepherd’s hut blends rustic charm with modern comfort, offering a king-sized stargazing bed, a cozy fire-lit deck, and a luxury bathroom, all set in a peaceful meadow.

Guest favorite
A clear, geodesic dome reveals a cozy pod interior, surrounded by greenery. An inviting wood-fired hot tub is positioned on a wooden deck, complemented by a dining area. Sunlight illuminates the pod, creating a warm and serene outdoor atmosphere.
Dome in West Horsley
4.94 out of 5 average rating, 392 reviews

Unique Dome | Glamping | Hot Tub | Surrey | Adults

Olive Pod is the ultimate cosy, private and picturesque geo dome retreat. Set on a fruit farm in Surrey, in its own secluded field behind tall fir trees, with no other pods or tents nearby. A firm favourite adults-only escape for proposals, anniversaries, birthdays and honeymoons - we can also decorate for your arrival ✨ The perfect place to unwind and recharge in a peaceful natural setting. Ideal for couples or friends. No infants, children or pets.

Guest favorite
Cottage in Privett
4.96 out of 5 average rating, 625 reviews

The Barn @ North Lodge -Soho Farmhouse-esque Cabin

Inspired by Soho Farmhouse. A stylish converted barn set in the grounds of a Georgian Lodge within the South Downs National Park. Conveniently located close to the picturesque market towns of Alresford, Petersfield, Alton and historic Winchester, it is an ideal base to both explore Hampshire and kick back and relax in luxury. Take a look at the Barn on ‘Escape to the Country’ series 25, Episode 10 on iPlayer!

Popular amenities for Medstead vacation rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Hampshire
  5. Medstead